Ortho-substituted 1-naphthyl ethers and fungicides containing these

ABSTRACT

Ortho-substituted 1-napthyl ethers of the formula ##STR1## where X is CH or N, Y is saturated or unsaturated alkylene and R is aryl, aryloxy, arylthio or arylalkoxy, the aromatic ring being substituted or unsubstituted, and fungicides containing these compounds.

The present invention relates to novel ortho-substituted 1-naphthylethers, the prepartion thereof, fungicides containing these, and the usethereof as fungicides.

The use of oxime ethers such as methyl 2-benzyloxyphenyl glyoxylateO-methyloxime as fungicides has been disclosed (EP 253213, 254426).However, their fungicidal action is often inadequate.

We have found that ortho-substituted 1-naphthyl ethers of the generalformula I ##STR2## where X is CH or N, Y is C₁ -C₁₂ -alkylene which canbe unsaturated and R is aryl, aryloxy, arylthio or arylalkoxy, it beingpossible for the aromatic ring to be substituted one to five times bythe following: halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₄-alkylthio, C₁ -C₂ -haloalkyl, aryl, aryl-C₁ -C₂ -alkoxy, C₁ -C₄-alkylcarbonyl, amino which is substituted once or twice by C₁ -C₄-alkyl, or cyano or nitro, have an excellent fungicidal action.

Examples of possible meanings of the radicals listed for the generalformula are the following:

X can be CH or N,

Y can be straight-chain C₁ -C₁₂ -alkylene, in particular C₁ -C₄-alkylene (e.g. methylene, ethylene, propylene, butylene, pentylene,hexylene, heptylene, octylene, nonylene, decylene), branched C₂ -C₁₂-alkylene (e.g. methylethylene) or C₄ -C₁₂ -alkenylene (e.g.butenylene),

R can be aryl (phenyl), aryloxy (phenoxy, 1-naphthyloxy, 2-naphthyloxy),arylthio (phenylthio) or arylalkoxy (benzyloxy), it being possible forthe aromatic ring to be substituted one to five (one to three) times bythe following:

halogen (e.g. fluorine, chlorine, bromine, iodine), C₁ -C₆ -alkyl (e.g.methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-, iso-,sec-, tert- or neo-pentyl, hexyl), C₁ -C₆ -alkoxy (e.g. methoxy, ethoxy,n- or iso-propoxy, n-, iso-, sec- or tert-butoxy), C₁ -C₄ -alkylthio(e.g. methylthio, ethylthio), C₁ -C₂ -haloalkyl (e.g. difluoromethyl,trifluoromethyl), aryl (e.g. phenyl), aryl-C₁ -C₂ -alkoxy (e.g.benzyloxy), C₁ -C₄ -alkylcarbonyl (e.g. acetyl), amino which issubstituted once or twice by C₁ -C₄ -alkyl (e.g. dimethylamino), orcyano or nitro.

The novel compounds of the formula I can, because of the C═N doublebond, result as E/Z isomer mixtures which can be separated in aconventional manner, e.g. by crystallization or chromatography, into theindividual components. Both the individual isomers and the mixturesthereof are embraced by the invention and can be used as fungicides.

The novel compounds of the general formula I can be prepared by thefollowing processes, for example:

starting from 1-naphthol it is possible by Friedel-Crafts acylation withmethyl oxalyl chloride in a suitable solvent (for exampledichloromethane) in the presence of a Lewis acid (for example titaniumtetrachloride) to synthesize the α-keto ester III which is known fromthe literature (O. Piccolo et al., Tetrahedron 42 (1986), 885-891).##STR3##

Starting from the compound of the formula III it is possible to obtainthe novel and valuable intermediates of the formula IV which arelikewise embraced by this invention and in which X is CH or N ##STR4##

The α-keto ester III can be converted into the novel oxime etherderivative of the formula IV (X═N) by reacting it withO-methylhydroxylamine, or by reacting first with hydroxylamine to givethe corresponding oxime and then with a methylating agent such as methyliodide or dimethyl sulfate (cf. EP 253213). ##STR5##

The α-keto ester III can be converted into the novel enol etherderivative of the formula IV (X═CH) by subjecting it to a Wittigreaction with methoxymethyltriphenylphosphonium halide (cf. EP 44448).##STR6##

The novel compounds of the general formula I can be prepared, forexample, by reacting the compound of the general formula IV with halidesof the formula II in a suitable solvent such as methanol orN,N-dimethylformamide by conventional processes (cf. Houben-Weyl,Methoden der organischen Chemie, volume 6/3, p. 54, Thieme-Verlag,Stuttgart 1965). ##STR7##

R, Y and X have the abovementioned meanings. Hal is Cl, Br or I.

The novel compounds of the general formula I can also be prepared, forexample, by reacting the α-keto ester of the formula III with halides ofthe formula II in a suitable solvent such as methanol orN,N-dimethylformamide by conventional processes (cf. Houben-Weyl,Methoden der organischen Chemie, volume 6/3, p. 54, Thieme-Verlag,Stuttgart 1965) to give the novel α-keto carboxylic esters of theformula V: ##STR8##

These esters of the general formula V can be converted into thecompounds of the general formula I according to the invention; reactionwith O-methylhydroxylamine or with hydroxylamine and subsequentmethylation with a methylating agent such as methyl iodide or dimethylsulfate result in the novel oxime ether derivatives of the formula I(X═N) (cf. EP 253213), and a Wittig reaction withmethoxymethyltriphenylphosphonium halide results in the novel enol etherderivatives of the formula I (X═CH) (cf. EP 44448).

The α-keto carboxylic esters of the formula V are novel and valuableintermediates and are likewise embraced by this invention.

The preparation of the novel compounds of the formulae I and IV isillustrated by the following examples:

Preparation Examples

a) 28.5 g (0.15 mol) of titanium tetrachloride are added under nitrogenat -10° C. to 150 ml of methylene chloride. This is followed by dropwiseaddition at -40° C. of, firstly, 22.3 g (0.15 mol) of 1-naphtholdissolved in 100 ml of methylene chloride and then 18.5 g (0.15 mol) ofmethyl oxalyl chloride. After stirring at this temperature for 30 min, alittle dilute hydrochloric acid is added at room temperature (20° C.),and the mixture is poured onto ice. The organic phase is washed 1× withH₂ O, dried over sodium sulfate and concentrated. 30 g (0.13 mol) ofmethyl 1-hydroxy-2-naphthylglyoxylate (87% yield) are obtained.

¹ H NMR (CDCl₃): δ=4.05 (s, 3H), 7.25 (d, 1H), 7.40-7.80 (m, 4H), 8.45(d, 1H), 13.00 (s, 1H).

b) 69 g (0.26 mol) of methyl 1-hydroxy-2-naphthylglyoxylate and 44 g(0.53 mol) of O-methylhydroxylamine hydrochloride in 800 ml of methanolare stirred under reflux for 6 h. The mixture is then concentrated; theresidue is taken up in ethyl acetate, and the solution is washed with H₂O, dried over sodium sulfate and concentrated again. 52 g (0.20 mol) ofmethyl 1-hydroxy-2-naphthylglyoxylate O-methyloxime (77% yield) areobtained.

¹ H NMR (CDCl₃): δ=4.00 (s, 3H), 4.05 (s, 3H), 7.00 (d, 1H), 7.30 (d,1H), 7.40-7.90 (m, 4H), 8.35 (m, 1H), 10.90 (s, 1H).

c) 5 g (19 mmol) of methyl 1-hydroxy-2-naphthylglyoxylate O-methyloxime,2.7 g (19 mmol) of 2-fluorobenzyl chloride and 2.6 g (19 mmol) ofpotassium carbonate in 65 ml of methanol are stirred under reflux for 8h. The mixture is cooled to room temperature and the solids are removedby filtration. The filtrate is concentrated, and dilute sodium hydroxidesolution is added. The mixture is then extracted by shaking severaltimes with ether; the combined ether phases are washed with H₂ O, driedover sodium sulfate and concentrated. 5 g (13.6 mmol) of methyl1-(2-fluorobenzyloxy)-2-naphthylglyoxylate O-methyloxime (yield 71%) areobtained (compound no. 2, Table 1).

¹ H NMR (CDCl₃): δ=3.65 (s, 3H), 4.10 (s, 3H), 5.10 (s, 2H), 7.00-8.20(m, 10H).

The following compounds are prepared in a corresponding manner.

                                      TABLE 1                                     __________________________________________________________________________     ##STR9##                                                                     Comp.                                                                         no.  R                 Y             mp (°C.)                                                                    IR (cm.sup.-1)                      __________________________________________________________________________    1    C.sub.6 H.sub.5   CH.sub.2      resin                                                                              2930, 1743, 1358, 1227, 1061,                                                 1036, 752                           2    2-FC.sub.6 H.sub.4                                                                              CH.sub.2      oil  2940, 1743, 1493, 1231, 1037,                                                 757                                 3    3-FC.sub.6 H.sub.4                                                                              CH.sub.2      resin                                                                              2950, 1743, 1358, 1263, 1037,                                                 752                                 4    4-FC.sub.6 H.sub.4                                                                              CH.sub.2      resin                                                                              2940, 1742, 1511, 1225, 1037,                                                 821                                 5    2,4-F.sub.2C.sub.6 H.sub.3                                                                      CH.sub.2      resin                                                                              2940, 1742, 1506, 1227, 1101,                                                 1037, 852                           6    2-ClC.sub.6 H.sub.4                                                                             CH.sub.2      resin                                                                              2940, 1743, 1358, 1226, 1037,                                                 753                                 7    3-ClC.sub.6 H.sub.4                                                                             CH.sub.2      resin                                                                              2940, 1742, 1356, 1226, 1037,                                                 752                                 8    4-ClC.sub.6 H.sub.4                                                                             CH.sub.2      resin                                                                              2940, 1743, 1357, 1227, 1037,                                                 810                                 9    2,4-Cl.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2      95   2940, 1733, 1474, 1231, 1098,                                                 1037, 815                           10   2,6-Cl.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2                                               11   3,5-Cl.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2                                               12   2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                   CH.sub.2                                               13   2-BrC.sub.6 H.sub.4                                                                             CH.sub.2      resin                                                                              2940, 1743, 1356, 1226, 1037,                                                 752                                 14   3-BrC.sub.6 H.sub.4                                                                             CH.sub.2      resin                                                                              2940, 1742, 1355, 1226, 1061,                                                 1036                                15   4-BrC.sub.6 H.sub.4                                                                             CH.sub.2      resin                                                                              2940, 1742, 1356, 1227, 1037,                                                 808                                 16   2,4-Br.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2                                               17   2-J-C.sub.6 H.sub.4                                                                             CH.sub.2      resin                                                                              2945, 1743, 1335, 1225, 1100,                                                 1062, 1037, 750                     18   2-CH.sub.3C.sub.6 H.sub.4                                                                       CH.sub.2      resin                                                                              2930, 1742, 1359, 1226, 1036,                                                 748                                 19   3-CH.sub.3C.sub.6 H.sub.4                                                                       CH.sub.2      resin                                                                              2940, 1743, 1355, 1226, 1037,                                                 752                                 20   4-CH.sub.3C.sub.6 H.sub.4                                                                       CH.sub.2      resin                                                                              2930, 1743, 1358, 1225, 1060,                                                 1037                                21   2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                             CH.sub. 2                                              22   2,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                             CH.sub.2      resin                                                                              2920, 1742, 1358, 1225, 1100,                                                 1061, 1036, 818                     23   2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                           CH.sub.2                                               24   4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                              CH.sub.2      resin                                                                              2962, 1745, 1356, 1226, 1100,                                                 1061, 1037, 817                     25   4-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                              CH.sub.2                                               26   4-C.sub.2 H.sub.5C.sub.6 H.sub.4                                                                CH.sub.2      resin                                                                              2950, 1743, 1358, 1225, 1061,                                                 1037, 819, 752                      27   2-CH.sub.3 OC.sub.6 H.sub.4                                                                     CH.sub.2                                               28   3-CH.sub.3 OC.sub.6 H.sub.4                                                                     CH.sub.2      resin                                                                              2930, 1742, 1357, 1265, 1227,                                                 1037                                29   4-CH.sub.3 OC.sub.6 H.sub.4                                                                     CH.sub.2                                               30   4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4                                                              CH.sub.2                                               31   4-i-C.sub.3 H.sub.7 OC.sub.6 H.sub.4                                                            CH.sub.2                                               32   2-CF.sub.3C.sub.6 H.sub.4                                                                       CH.sub.2                                               33   3-CF.sub.3C.sub.6 H.sub.4                                                                       CH.sub.2      resin                                                                              1940, 1743, 1331, 1166, 1126,                                                 1037                                34   4-CF.sub.3C.sub.6 H.sub. 4                                                                      CH.sub.2                                               35   2-CNC.sub.6 H.sub.4                                                                             CH.sub.2      81-85                                                                              2940, 2230, 1742, 1360, 1228,                                                 1036, 764                           36   3-CNC.sub.6 H.sub.4                                                                             CH.sub.2      resin                                                                              2940, 2225, 1741, 1358, 1229,                                                 1036, 796                           37   4-CNC.sub.6 H.sub.4                                                                             CH.sub.2      resin                                                                              2930, 2220, 1741, 1359, 1228,                                                 1036, 819                           38   2-NO.sub.2C.sub.6 H.sub.4                                                                       CH.sub.2                                               39   3-NO.sub.2C.sub.6 H.sub.4                                                                       CH.sub.2      resin                                                                              2940, 1737, 1531, 1350, 1229,                                                 1038, 730                           40   4-NO.sub.2C.sub.6 H.sub.4                                                                       CH.sub.2                                               41   3-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                CH.sub.2                                               42   4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                                CH.sub.2                                               43   4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                              CH.sub.2                                               44   2-F, 3-CH.sub.3C.sub.6 H.sub.3                                                                  CH.sub.2                                               45   2-Cl, 3-CH.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2      resin                                                                              2940, 1743, 1354, 1225, 1102,                                                 1063, 1037, 772                     46   2-Br, 3-CH.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2      109  2935, 1738, 1353, 1225, 1102,                                                 1062, 1032, 772                     47   2-Cl, 3-i-C.sub.3 H.sub. 7C.sub.6 H.sub.3                                                       CH.sub.2      resin                                                                              2964, 1744, 1355, 1225, 1102,                                                 1063, 1037, 756                     48   2-CH.sub.3, 3-i-C.sub.3 H.sub.7C.sub.6 H.sub.3                                                  CH.sub.2                                               49   2-CH.sub.3, 3-C.sub.6 H.sub.5C.sub.6 H.sub.3                                                    CH.sub.2                                               50   2-Cl, 3-C.sub.6 H.sub.5C.sub.6 H.sub.3                                                          CH.sub.2                                               51   2-CH.sub.3 O, 3-i-C.sub.3 H.sub.7C.sub.6 H.sub.3                                                CH.sub.2                                               52   2,4,5-Cl.sub.3C.sub.6 H.sub.2                                                                   CH.sub.2                                               53   2,4,5-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                           CH.sub.2                                               54   2-CH.sub.3 O, 5-NO.sub.2C.sub.6 H.sub.3                                                         CH.sub.2                                               55   2,5-Cl.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2                                               56   2,5-F.sub.2C.sub.6 H.sub.3                                                                      CH.sub.2                                               57   2-Cl, 5-CH.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2                                               58   2-F, 3-CH.sub.3C.sub.6 H.sub.3                                                                  CH.sub.2                                               59   2,3-F.sub.2C.sub.6 H.sub.3                                                                      CH.sub.2                                               60   2,3-Cl.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2                                               61   2-F, 3-ClC.sub.6 H.sub.3                                                                        CH.sub.2                                               62   2-F, 4-Br C.sub.6 H.sub.3                                                                       CH.sub.2                                               63   2,6-F.sub.2C.sub.6 H.sub.3                                                                      CH.sub.2                                               64   2-F, 6-ClC.sub.6 H.sub.3                                                                        CH.sub.2                                               65   2-Cl, 6-CF.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2                                               66   2,3,4,5,6-(CH.sub.3).sub.5C.sub.6                                                               CH.sub.2                                               67   2,3,4,5,6-F.sub.5C.sub.6                                                                        CH.sub.2                                               68   2-CH.sub.3, 4-ClC.sub.6 H.sub.3                                                                 CH.sub.2                                               69   2-Cl, 4-CH.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2                                               70   2-CH.sub.3 O, 4-CH.sub.3C.sub.6 H.sub.3                                                         CH.sub.2                                               71   4-CH.sub.3 O, 2-CH.sub.3C.sub.6 H.sub.3                                                         CH.sub.2                                               72   C.sub.6 H.sub.5O  CH.sub.2CH.sub.2                                       73   2-FC.sub.6 H.sub.4O                                                                             CH.sub.2CH.sub.2                                       74   3-FC.sub.6 H.sub.4O                                                                             CH.sub.2CH.sub.2                                       75   4-FC.sub.6 H.sub.4O                                                                             CH.sub.2CH.sub.2                                       76   2-ClC.sub.6 H.sub.4O                                                                            CH.sub.2CH.sub.2                                       77   3-ClC.sub.6 H.sub.4O                                                                            CH.sub.2CH.sub.2                                       78   4-Cl C.sub.6 H.sub.4O                                                                           CH.sub.2CH.sub.2                                       79   2-CH.sub.3C.sub.6 H.sub.4O                                                                      CH.sub.2CH.sub.2                                       80   3-CH.sub.3C.sub.6 H.sub.4O                                                                      CH.sub.2CH.sub.2                                       81   4-CH.sub.3C.sub.6 H.sub.4O                                                                      CH.sub.2CH.sub.2                                       82   2-CH.sub.3 OC.sub.6 H.sub.4O                                                                    CH.sub.2CH.sub.2                                       83   3-CH.sub.3 OC.sub.6 H.sub.4O                                                                    CH.sub.2CH.sub.2                                       84   4-CH.sub.3 OC.sub.6 H.sub.4O                                                                    CH.sub.2CH.sub.2                                       85   4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             CH.sub.2CH.sub.2                                       86   4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                             CH.sub.2CH.sub.2                                       87   4-CF.sub.3C.sub.6 H.sub.4O                                                                      CH.sub.2CH.sub.2                                       88   4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                               CH.sub.2CH.sub.2                                       89   4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                    CH.sub.2CH.sub.2                                       90   2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                  CH.sub.2CH.sub.2                                       91   2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          CH.sub.2CH.sub.2                                       92   1-naphthyl-O      CH.sub.2CH.sub.2                                       93   2-naphthyl-O      CH.sub.2CH.sub.2                                       94   2-BrC.sub.6 H.sub.4O                                                                            CH.sub.2CH.sub.2                                       95   3-BrC.sub.6 H.sub.4O                                                                            CH.sub.2CH.sub.2                                       96   4-BrC.sub.6 H.sub.4O                                                                            CH.sub.2CH.sub.2                                       97   2-CF.sub.3C.sub.6 H.sub.4O                                                                      CH.sub.2CH.sub.2                                       98   3-CF.sub.3C.sub.6 H.sub.4O                                                                      CH.sub.2CH.sub.2                                       99   4-CNC.sub.6 H.sub.4O                                                                            CH.sub.2CH.sub.2                                       100  4-CH.sub.3 COC.sub.6 H.sub.4O                                                                   CH.sub.2CH.sub.2                                       101  3-(CH.sub.3).sub.2 NC.sub.6 H.sub.4O                                                            CH.sub.2CH.sub.2                                       102  4-CH.sub.3 SC.sub.6 H.sub.4O                                                                    CH.sub.2CH.sub.2                                       103  2-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                             CH.sub.2CH.sub.2                                       104  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             CH.sub.2CH.sub.2                                       105  2,4-Cl.sub.2H.sub.6 H.sub.3O                                                                    CH.sub.2CH.sub.2                                       106  3,4-Cl.sub.2C.sub.6 H.sub.3O                                                                    CH.sub.2CH.sub.2                                       107  2,5-Cl.sub.2C.sub.6 H.sub.3O                                                                    CH.sub.2CH.sub.2                                       108  2,6-Cl.sub.2C.sub.6 H.sub.3O                                                                    CH.sub.2CH.sub.2                                       109  2,4,5-Cl.sub.3C.sub.6 H.sub.2O                                                                  CH.sub.2CH.sub.2                                       110  2-Cl, 4-FC.sub.6 H.sub.3O                                                                       CH.sub.2CH.sub.2                                       111  2-Cl, 4-BrC.sub.6 H.sub.3O                                                                      CH.sub.2CH.sub.2                                       112  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                            CH.sub.2CH.sub.2                                       113  2-CH.sub.3, 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.3O                                                 CH.sub.2CH.sub.2                                       114  2-CH.sub.3, 4-ClC.sub.6 H.sub.3O                                                                CH.sub.2CH.sub.2                                       115  2-CH.sub.3, 4,6-Cl.sub.2C.sub.6 H.sub.2O                                                        CH.sub.2CH.sub.2                                       116  2,6-(CH.sub.3).sub.2C.sub.6 H.sub. 3O                                                           CH.sub.2CH.sub.2                                       117  2,5,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          CH.sub.2CH.sub.2                                       118  2,4,5-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          CH.sub.2CH.sub.2                                       119  2-i-C.sub.3 H.sub.7, 5-CH.sub.3C.sub.6 H.sub.3O                                                 CH.sub.2CH.sub.2                                       120  3,5-(C.sub.2 H.sub.5).sub.2C.sub.6 H.sub.3O                                                     CH.sub.2CH.sub.2                                       121  2,4,6-(sec-C.sub.4 H.sub.9).sub.3C.sub.6 H.sub.2O                                               CH.sub.2CH.sub.2                                       122  3,5-(CH.sub.3 O).sub.2C.sub.6 H.sub.3O                                                          CH.sub.2CH.sub.2                                       123  2-CH.sub.3 O, 4-CH.sub.3C.sub.6 H.sub.3O                                                        CH.sub.2CH.sub.2                                       124  2,6-(CH.sub.3).sub.2, 4-CH.sub.3 SC.sub.6 H.sub.2O                                              CH.sub.2CH.sub.2                                       125  2-Cl, 5-CH.sub.3 OC.sub.6 H.sub.3O                                                              CH.sub.2CH.sub.2                                       126  2-CH.sub.3, 4-CH.sub.3 SC.sub.6 H.sub.3O                                                        CH.sub.2CH.sub.2                                       127  2,6-(CH.sub.3 O).sub.2C.sub.6 H.sub.3O                                                          CH.sub.2CH.sub.2                                       128  2-Cl, 4-C.sub.6 H.sub.5C.sub.6 H.sub.3O                                                         CH.sub.2CH.sub.2                                       129  2,Cl, 4-CH.sub.3C.sub.6 H.sub.3O                                                                CH.sub.2CH.sub.2                                       130  2-CH.sub.3, 6-i-C.sub.3 H.sub.7C.sub.6 H.sub.3O                                                 CH.sub.2CH.sub.2                                       131  3-t-C.sub.4 H.sub.9, 4-CH.sub.3 OC.sub.6 H.sub.3O                                               CH.sub.2CH.sub.2                                       132  2,4-(CH.sub.3).sub.2 -1-naphthyl-O                                                              CH.sub.2CH.sub.2                                       133  C.sub.6 H.sub.5S  CH.sub.2CH.sub.2                                       134  4-ClC.sub.6 H.sub.4S                                                                            CH.sub.2CH.sub.2                                       135  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                  CH.sub.2CH(CH.sub.3)                                   136  C.sub.6 H.sub.5O  CH.sub.2CH(CH.sub.3)                                   137  C.sub.6 H.sub.5O  (CH.sub.2).sub.3                                       138  2-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.3                                       139  3-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.3                                       140  4-FC.sub.6 H.sub.4 O                                                                            (CH.sub.2).sub.3                                       141  2-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.3                                       142  3-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.3                                       143  4-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.3                                       144  2-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.3                                       145  3-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.3                                       146  4-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.3                                       147  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.3                                       148  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.3                                       149  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.3                                       150  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             (CH.sub.2).sub.3                                       151  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                             (CH.sub.2).sub.3                                       152  4-CF.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.3                                       153  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                               (CH.sub.2).sub.3                                       154  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                    (CH.sub.2).sub.3                                       155  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                  (CH.sub.2).sub.3                                       156  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          (CH.sub.2).sub.3                                       157  1-naphthyl-O      (CH.sub.2).sub.3                                       158  2-naphthyl-O      (CH.sub.2).sub.3                                       159  2,4-Cl.sub.2C.sub.6 H.sub.3O                                                                    (CH.sub.2).sub.3                                       160  3,5-Cl.sub.2C.sub.6 H.sub.3O                                                                    (CH.sub.2).sub.3                                       161  3,4-Cl.sub.2C.sub.6 H.sub.3O                                                                    (CH.sub.2).sub.3                                       162  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                            (CH.sub.2).sub.3                                       163  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                            (CH.sub.3).sub.3                                       164  3-CF.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.3                                       165  2-Cl, 4-CH.sub.3C.sub.6 H.sub.3O                                                                (CH.sub.2).sub.3                                       166  C.sub.6 H.sub.5S  (CH.sub.2).sub. 3                                      167  C.sub.6 H.sub.5CH.sub.2O                                                                        (CH.sub.2).sub.3                                       168  C.sub.6 H.sub.5O  (CH.sub.2).sub.4                                       169  2-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.4                                       170  3-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.4                                       171  4-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.4                                       172  2-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.4                                       173  3-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.4                                       174  4-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.4                                       175  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.4                                       176  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.4                                       177  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.4                                       178  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             (CH.sub.2).sub.4                                       179  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                             (CH.sub.2).sub.4                                       180  4-CF.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.4                                       181  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                               (CH.sub.2).sub.4                                       182  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4                                                     (CH.sub.2).sub.4                                       183  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                  (CH.sub.2).sub.4                                       184  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          (CH.sub.2).sub.4                                       185  1-naphthyl-O      (CH.sub.2).sub.4                                       186  2-naphthyl-O      (CH.sub.2).sub.4                                       187  3-CF.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.4                                       188  3-iso-C.sub.3 H.sub.7C.sub.6 H.sub.4O                                                           (CH.sub.2).sub.4                                       189  4-iso-C.sub.3 H.sub.7C.sub.6 H.sub.4O                                                           (CH.sub.2).sub.4                                       190  3-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             (CH.sub.2).sub.4                                       191  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             (CH.sub.2).sub.4                                       192  3-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                               (CH.sub.2).sub.4                                       193  2,4-Cl.sub.2C.sub.6 H.sub.3O                                                                    (CH.sub.2).sub.4                                       194  3,4-Cl.sub.2C.sub.6 H.sub.3O                                                                    (CH.sub.2).sub.4                                       195  3,5-Cl.sub.2C.sub.6 H.sub.3O                                                                    (CH.sub.2).sub.4                                       196  2,6-Cl.sub.2C.sub.6 H.sub.3O                                                                    (CH.sub.2).sub.4                                       197  2-Cl, 4-CH.sub.3C.sub.6 H.sub.3O                                                                (CH.sub.2).sub.4                                       198  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                            (CH.sub.2).sub.4                                       199  2,5-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                            (CH.sub.2).sub.4                                       200  4-CNC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.4                                       201  C.sub.6 H.sub.5S  (CH.sub.2).sub.4                                       202  C.sub.6 H.sub.5CH.sub.2O                                                                        (CH.sub.2).sub.4                                       203  C.sub.6 H.sub.5O  CH.sub.2CHCHCH.sub.2                                   204  2-FC.sub.6 H.sub.4O                                                                             CH.sub.2CHCHCH.sub.2                                   205  3-FC.sub.6 H.sub.4O                                                                             CH.sub.2CHCHCH.sub.2                                   206  4-FC.sub.6 H.sub.4O                                                                             CH.sub.2CHCHCH.sub.2                                   207  2-ClC.sub.6 H.sub.4O                                                                            CH.sub.2CHCHCH.sub.2                                   208  3-ClC.sub.6 H.sub.4O                                                                            CH.sub.2CHCHCH.sub.2                                   209  4-ClC.sub.6 H.sub.4O                                                                            CH.sub.2CHCHCH.sub.2                                   210  C.sub.6 H.sub.5O  (CH.sub.2).sub.5                                       211  2-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.5                                       212  3-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.5                                       213  4-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.5                                       214  2-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.5                                       215  3-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.5                                       216  4-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.5                                       217  2-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.5                                       218  3-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.5                                       219  4-CH.sub.3C.sub.6 H.sub.4O                                                                       (CH.sub.2).sub.5                                      220  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.5                                       221  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.5                                       222  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.5                                       223  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             (CH.sub.2).sub.5                                       224  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                             (CH.sub.2).sub.5                                       225  4-CF.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.5                                       226  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                               (CH.sub.2).sub.5                                       227  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                    (CH.sub.2).sub.5                                       228  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                  (CH.sub.2).sub.5                                       229  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          (CH.sub.2).sub.5                                       230  1-naphthyl-O      (CH.sub.2).sub.5                                       231  2-naphthyl-O      (CH.sub.2).sub.5                                       232  C.sub.6 H.sub.5CH.sub.2O                                                                        (CH.sub.2).sub. 5                                      233  C.sub.6 H.sub.5O  (CH.sub.2).sub.6                                       234  2-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.6                                       235  3-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.6                                       236  4-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.6                                       237  2-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.6                                       238  3-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.6                                       239  4-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.6                                       240  2-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.6                                       241  3-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.6                                       242  4-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.6                                       243  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.6                                       244  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.6                                       245  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.6                                       246  4-t-C.sub.4 H.sub.9C.sub.6 H.sub. 4O                                                            (CH.sub.2).sub.6                                       247  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                             (CH.sub.2).sub.6                                       248  4-CF.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.6                                       249  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                               (CH.sub.2).sub.6                                       250  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                    (CH.sub.2).sub.6                                       251  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                  (CH.sub.2).sub.6                                       252  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          (CH.sub.2).sub.6                                       253  1-naphthyl-O      (CH.sub.2).sub.6                                       254  2-naphthyl-O      (CH.sub.2).sub.6                                       255  C.sub.6 H.sub.5CH.sub.2O                                                                        (CH.sub.2).sub.6                                       256  C.sub.6 H.sub.5O  (CH.sub.2).sub.7                                       257  2-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.7                                       258  3-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.7                                       259  4-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.7                                       260  2-FC.sub. 6 H.sub.4O                                                                            (CH.sub.2).sub.7                                       261  3-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.7                                       262  4-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.7                                       263  2-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.7                                       264  3-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.7                                       265  4-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.7                                       266  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.7                                       267  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.7                                       268  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.7                                       269  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             (CH.sub.2).sub.7                                       270  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                             (CH.sub.2).sub.7                                       271  4-CF.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.7                                       272  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                               (CH.sub.2).sub.7                                       273  2,4,6-(Cl.sub.3).sub.3C.sub.6 H.sub.2O                                                          (CH.sub.2).sub.7                                       274  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          (CH.sub.2).sub.7                                       275  1-naphthyl-O      (CH.sub.2).sub.7                                       276  2-naphthyl-O      (CH.sub.2).sub.7                                       277  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                    (CH.sub.2).sub.7                                       278  C.sub.6 H.sub.5CH.sub.2O                                                                        (CH.sub.2).sub.7                                       279  C.sub.6 H.sub.5O  (CH.sub.2).sub.8                                       280  2-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.8                                       281  3-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.8                                       282  4-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.8                                       283  2-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.8                                       284  3-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.8                                       285  4-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.8                                       286  2-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.8                                       287  3-CH.sub.3 C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.8                                       288  4-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.8                                       289  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.8                                       290  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.8                                       291  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.8                                       292  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             (CH.sub.2).sub.8                                       293  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                             (CH.sub.2).sub.8                                       294  4-CF.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.8                                       295  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                               (CH.sub.2).sub.8                                       296  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                    (CH.sub.2).sub.8                                       297  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                  (CH.sub.2).sub.8                                       298  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          (CH.sub.2).sub.8                                       299  1-naphthyl-O      (CH.sub.2 ).sub.8                                      300  2-naphthyl-O      (CH.sub.2).sub.8                                       301  C.sub.6 H.sub.5CH.sub.2O                                                                        (CH.sub.2).sub.8                                       302  C.sub.6 H.sub.5O  (CH.sub.2).sub.9                                       303  C.sub.6 H.sub.5O  (CH.sub.2).sub.10                                      304  2-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.10                                      305  3-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.10                                      306  4-ClC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.10                                      307  2-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.10                                      308  3-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.10                                      309  4-FC.sub.6 H.sub.4O                                                                             (CH.sub.2).sub.10                                      310  2-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.10                                      311  3-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.10                                      312  4-CH.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.10                                      313  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.10                                      314  3-CH.sub. 3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.10                                      315  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                    (CH.sub.2).sub.10                                      316  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                             (CH.sub.2).sub.10                                      317  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                             (CH.sub.2).sub.10                                      318  4-CF.sub.3C.sub.6 H.sub.4O                                                                      (CH.sub.2).sub.10                                      319  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                               (CH.sub.2).sub.10                                      320  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                    (CH.sub.2).sub.10                                      321  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                  (CH.sub.2).sub.10                                      322  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                          (CH.sub.2).sub.10                                      323  1-naphthyl-O      (CH.sub.2).sub.10                                      324  2-naphthyl-O      (CH.sub.2).sub.10                                      325  C.sub.6 H.sub.5CH.sub.2O                                                                        (CH.sub.2).sub.10                                      326  3,4-Cl.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2      resin                                                                              2945, 1742, 1473, 1353, 1228,                                                 1061, 1035, 819                     327  3-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                              CH.sub.2                                               328  4-C.sub.12H.sub.25C.sub.6 H.sub.4                                                               CH.sub.2                                               329  2-Cl, 6-CNC.sub.6 H.sub.3                                                                       CH.sub.2                                               330  3,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                             CH.sub.2                                               331  2-CH.sub.3, 4-t-C.sub.4 H.sub.9C.sub.6 H.sub.3                                                  CH.sub.2                                               332  2-Cl, 4-CH.sub.3 OC.sub.6 H.sub.3                                                               CH.sub.2                                               333  2,3,6-Cl.sub.3C.sub.6 H.sub.2                                                                   CH.sub.2                                               __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________     ##STR10##                                                                    Comp. no.                                                                           R                Y             mp(°C.)                                                                     IR(cm.sup.-1)                       __________________________________________________________________________    1a    C.sub.6 H.sub.5  CH.sub.2                                               2a    2-FC.sub.6 H.sub.4                                                                             CH.sub.2                                               3a    3-FC.sub.6 H.sub.4                                                                             CH.sub.2                                               4a    4-FC.sub.6 H.sub.4                                                                             CH.sub.2                                               5a    2,4-F.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2                                               6a    2-ClC.sub.6 H.sub.4                                                                            CH.sub.2                                               7a    3-ClC.sub.6 H.sub.4                                                                            CH.sub.2                                               8a    4-ClC.sub.6 H.sub.4                                                                            CH.sub.2                                               9a    2,4-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.2                                               10a   2,6-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.2                                               11a   3,5-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.2                                               12a   2,4,6-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.2                                               13a   2-BrC.sub.6 H.sub.4                                                                            CH.sub.2                                               14a   3-BrC.sub.6 H.sub.4                                                                            CH.sub.2                                               15a   4-BrC.sub.6 H.sub.4                                                                            CH.sub.2                                               16a   2,4-Br.sub.2C.sub.6 H.sub.3                                                                    CH.sub.2                                               17a   2-JC.sub.6 H.sub.4                                                                             CH.sub.2                                               18a   2-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.2                                               19a   3-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.2                                               20a   4-CH.sub.3C.sub.6 H.sub.4                                                                      CH.sub.2                                               21a   2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.2                                               22a   2,5-(CH.sub.3).sub.2C.sub.6 H.sub.3                                                            CH.sub.2                                               23a   2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.2                                               24a   4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4                                                             CH.sub.2                                               25a   4-i-C.sub.3 H.sub.7C.sub.6 H.sub.4                                                             CH.sub.2                                               26a   4-C.sub.2 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.2                                               27a   2-CH.sub.3 OC.sub.6 H.sub.4                                                                    CH.sub.2                                               28a   3-CH.sub.3 OC.sub.6 H.sub.4                                                                    CH.sub.2                                               29a   4-CH.sub.3 OC.sub.6 H.sub.4                                                                    CH.sub.2                                               30a   4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.2                                               31a   4-i-C.sub.3 H.sub.7 OC.sub.6 H.sub.4                                                           CH.sub.2                                               32a   2-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.2                                               33a   3-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.2                                               34a   4-CF.sub.3C.sub.6 H.sub.4                                                                      CH.sub.2                                               35a   2-CNC.sub.6 H.sub.4                                                                            CH.sub.2                                               36a   3-CNC.sub.6 H.sub.4                                                                            CH.sub.2                                               37a   4-CNC.sub.6 H.sub.4                                                                            CH.sub.2                                               38a   2-NO.sub.2C.sub.6 H.sub.4                                                                      CH.sub.2                                               39a   3-NO.sub.2C.sub.6 H.sub.4                                                                      CH.sub.2                                               40a   4-NO.sub.2C.sub.6 H.sub.4                                                                      CH.sub.2                                               41a   3-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.2                                               42a   4-C.sub.6 H.sub.5C.sub.6 H.sub.4                                                               CH.sub.2                                               43a   4-C.sub.6 H.sub.5 OC.sub.6 H.sub.4                                                             CH.sub.2                                               44a   2-F,3-CH.sub.3C.sub.6 H.sub.3                                                                  CH.sub.2                                               45a   2-Cl,3-CH.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2                                               46a   2-Br,3-CH.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2                                               47a   2-Cl,3-i-C.sub.3 H.sub.7C.sub.6 H.sub.3                                                        CH.sub.2                                               48a   2-CH.sub.3,3-i-C.sub.3 H.sub.7C.sub.6 H.sub.3                                                   CH.sub.2                                              49a   2-CH.sub.3,3-C.sub.6 H.sub.5C.sub.6 H.sub.3                                                    CH.sub.2                                               50a   2-Cl,3-C.sub.6 H.sub.5C.sub.6 H.sub.3                                                          CH.sub.2                                               51a   2-CH.sub.3 O,3-i-C.sub.3 H.sub.7C.sub.6 H.sub.3                                                CH.sub.2                                               52a   2,4,5-Cl.sub.3C.sub.6 H.sub.2                                                                  CH.sub.2                                               53a   2,4,5-(CH.sub.3).sub.3C.sub.6 H.sub.2                                                          CH.sub.2                                               54a   2-CH.sub.3 O,5-NO.sub.2C.sub.6 H.sub.3                                                         CH.sub.2                                               55a   2,5-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.2                                               56a   2,5-F.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2                                               57a   2-Cl,5-CH.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2                                               58a   2-F,3-CH.sub.3C.sub.6 H.sub.3                                                                  CH.sub.2                                               59a   2,3-F.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2                                               60a   2,3-Cl.sub.2C.sub.6 H.sub.3                                                                    CH.sub.2                                               61a   2-F,3-ClC.sub.6 H.sub.3                                                                        CH.sub.2                                               62a   2-F,4-BrC.sub.6 H.sub.3                                                                        CH.sub.2                                               63a   2,6-F.sub.2C.sub.6 H.sub.3                                                                     CH.sub.2                                               64a   2-F,6-ClC.sub.6 H.sub.3                                                                        CH.sub.2                                               65a   2-Cl,6-CF.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2                                               66a   2,3,4,5,6-(CH.sub.3).sub.5C.sub.6                                                              CH.sub.2                                               67a   2,3,4,5,6-F.sub.5C.sub.6                                                                       CH.sub.2                                               68a   2-CH.sub.3,4-ClC.sub.6 H.sub.3                                                                 CH.sub.2                                               69a   2-Cl,4-CH.sub.3C.sub.6 H.sub.3                                                                 CH.sub.2                                               70a   2-CH.sub.3 O,4-CH.sub.3C.sub.6 H.sub.3                                                         CH.sub.2                                               71a   4-CH.sub.3 O,2-CH.sub.3C.sub.6 H.sub.3                                                         CH.sub.2                                               72a   C.sub.6 H.sub.5O CH.sub.2CH.sub.2                                       73a   2-FC.sub.6 H.sub.4O                                                                            CH.sub.2CH.sub.2                                       74a   3-FC.sub.6 H.sub.4O                                                                            CH.sub.2CH.sub.2                                       75a   4-FC.sub.6 H.sub.4O                                                                            CH.sub.2CH.sub.2                                       76a   2-ClC.sub.6 H.sub.4O                                                                           CH.sub.2CH.sub.2                                       77a   3-ClC.sub.6 H.sub.4O                                                                           CH.sub.2CH.sub.2                                       78a   4-ClC.sub.6 H.sub.4O                                                                           CH.sub.2CH.sub.2                                       79a   2-CH.sub.3C.sub.6 H.sub.4O                                                                     CH.sub.2CH.sub.2                                       80a   3-CH.sub.3C.sub.6 H.sub.4O                                                                     CH.sub.2CH.sub.2                                       81a   4-CH.sub.3 C.sub.6 H.sub.4O                                                                    CH.sub.2CH.sub.2                                       82a   2-CH.sub.3 OC.sub.6 H.sub.4O                                                                   CH.sub.2CH.sub.2                                       83a   3-CH.sub.3 OC.sub.6 H.sub.4O                                                                   CH.sub.2CH.sub.2                                       84a   4-CH.sub.3 OC.sub.6 H.sub.4O                                                                   CH.sub.2CH.sub.2                                       85a   4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            CH.sub.2CH.sub.2                                       86a   4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                            CH.sub.2CH.sub.2                                       87a   4-CF.sub.3C.sub.6 H.sub.4O                                                                     CH.sub.2CH.sub.2                                       88a   4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                              CH.sub.2CH.sub.2                                       89a   4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                   CH.sub.2CH.sub.2                                       90a   2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                 CH.sub.2CH.sub.2                                       91a   2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                         CH.sub.2CH.sub.2                                       92a   1-naphthyl-O     CH.sub.2CH.sub.2                                       93a   2-naphthyl-O     CH.sub.2CH.sub.2                                       94a   2-BrC.sub.6 H.sub.4O                                                                           CH.sub.2CH.sub.2                                       95a   3-BrC.sub.6 H.sub.4O                                                                           CH.sub.2CH.sub.2                                       96a   4-BrC.sub.6 H.sub.4O                                                                           CH.sub.2CH.sub.2                                       97a   2-CF.sub.3C.sub.6 H.sub.4O                                                                     CH.sub.2CH.sub.2                                       98a   3-CF.sub.3C.sub.6 H.sub.4O                                                                     CH.sub.2CH.sub.2                                       99a   4-CNC.sub.6 H.sub.4O                                                                           CH.sub.2CH.sub.2                                       100a  4-CH.sub.3 COC.sub.6 H.sub.4O                                                                  CH.sub.2CH.sub.2                                       101a  3-(CH.sub.3).sub.2 NC.sub.6 H.sub.4O                                                           CH.sub.2CH.sub.2                                       102a  4-CH.sub.3 SC.sub.6 H.sub.4O                                                                   CH.sub.2CH.sub.2                                       103a  2-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                            CH.sub.2CH.sub.2                                       104a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            CH.sub.2CH.sub.2                                       105a  2,4-Cl.sub.2H.sub.6 H.sub.3O                                                                   CH.sub.2CH.sub.2                                       106a  3,4-Cl.sub.2C.sub.6 H.sub.3O                                                                   CH.sub.2CH.sub.2                                       107a  2,5-Cl.sub.2C.sub.6 H.sub.3O                                                                   CH.sub.2CH.sub.2                                       108a  2,6-Cl.sub.2C.sub.6 H.sub.3O                                                                   CH.sub.2CH.sub.2                                       109a  2,4,5-Cl.sub.3C.sub.6 H.sub.2O                                                                 CH.sub.2CH.sub.2                                       110a  2-Cl,4-FC.sub.6 H.sub.3O                                                                       CH.sub.2CH.sub.2                                       111a  2-Cl,4-BrC.sub.6 H.sub.3O                                                                      CH.sub.2CH.sub.2                                       112a  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                           CH.sub.2CH.sub.2                                       113a  2-CH.sub.3,4-t-C.sub.4 H.sub.9C.sub.6 H.sub.3O                                                 CH.sub.2CH.sub.2                                       114a  2-CH.sub.3,4-ClC.sub.6 H.sub.3O                                                                CH.sub.2CH.sub.2                                       115a  2-CH.sub.3,4,6-Cl.sub.2C.sub.6 H.sub.2O                                                        CH.sub.2CH.sub.2                                       116a  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                           CH.sub.2CH.sub.2                                       117a  2,5,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                         CH.sub.2CH.sub.2                                       118a  2,4,5-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                         CH.sub.2CH.sub.2                                       119a  2-i-C.sub.3 H.sub.7,5-CH.sub.3 C.sub.6 H.sub.3O                                                CH.sub.2CH.sub.2                                       120a  3,5-(C.sub.2 H.sub.5).sub.2C.sub.6 H.sub.3O                                                    CH.sub.2CH.sub.2                                       121a  2,4,6-(sec-C.sub.4 H.sub.9).sub.3C.sub.6 H.sub.2O                                              CH.sub.2CH.sub.2                                       122a  3,5-(CH.sub.3 O).sub.2C.sub.6 H.sub.3O                                                         CH.sub.2CH.sub.2                                       123a  2-CH.sub.3 O,4-CH.sub.3C.sub.6 H.sub.3O                                                        CH.sub.2CH.sub.2                                       124a  2,6-(CH.sub.3).sub.2,4-CH.sub.3 SC.sub.6 H.sub.2O                                              CH.sub.2CH.sub.2                                       125a  2-Cl,5-CH.sub.3 OC.sub.6 H.sub.3O                                                              CH.sub.2CH.sub.2                                       126a  2-CH.sub.3,4-CH.sub.3 SC.sub.6 H.sub.3O                                                        CH.sub.2CH.sub.2                                       127a  2,6-(CH.sub.3 O).sub.2C.sub.6 H.sub.3O                                                         CH.sub.2CH.sub.2                                       128a  2-Cl,4-C.sub.6 H.sub.5C.sub.6 H.sub.3O                                                         CH.sub.2CH.sub.2                                       129a  2-Cl,4-CH.sub.3C.sub.6 H.sub.3O                                                                CH.sub.2CH.sub.2                                       130a  2-CH.sub.3,6-i-C.sub.3 H.sub.7C.sub.6 H.sub.3O                                                 CH.sub.2CH.sub.2                                       131a  3-t-C.sub.4 H.sub.9,4-CH.sub.3 OC.sub.6 H.sub.3O                                               CH.sub.2CH.sub.2                                       132a  2,4-(CH.sub.3).sub.2 -1-naphthyl-O                                                             CH.sub.2CH.sub.2                                       133a  C.sub.6 H.sub.5S CH.sub.2CH.sub.2                                       134a  4-ClC.sub.6 H.sub.4S                                                                           CH.sub.2CH.sub.2                                       135a  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                 CH.sub.2CH(CH.sub.3)                                   136a  C.sub.6 H.sub.5O CH.sub.2CH(CH.sub.3)                                   137a  C.sub.6 H.sub.5O (CH.sub.2).sub.3                                       138a  2-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.3                                       139a  3-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.3                                       140a  4-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.3                                       141a  2-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.3                                       142a  3-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.3                                       143a  4-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.3                                       144a  2-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.3                                       145a  3-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.3                                       146a  4-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.3                                       147a  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.3                                       148a  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.3                                       149a  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.3                                       150a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            (CH.sub.2).sub.3                                       151a  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                            (CH.sub.2).sub.3                                       152a  4-CF.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.3                                       153a  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                              (CH.sub.2).sub.3                                       154a  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                   (CH.sub.2).sub.3                                       155a  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                 (CH.sub.2).sub.3                                       156a  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                         (CH.sub.2 ).sub.3                                      157a  1-naphthyl-O     (CH.sub.2).sub.3                                       158a  2-naphthyl-O     (CH.sub.2).sub.3                                       159a  2,4-Cl.sub.2C.sub.6 H.sub.3O                                                                   (CH.sub.2).sub.3                                       160a  3,5-Cl.sub.2C.sub.6 H.sub.3O                                                                   (CH.sub.2).sub.3                                       161a  3,4-Cl.sub.2C.sub.6 H.sub.3O                                                                   (CH.sub.2).sub.3                                       162a  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                           (CH.sub.2).sub.3                                       163a  2,4-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                           (CH.sub.2).sub.3                                       164a  3-CF.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.3                                       165a  2-Cl,4-CH.sub.3C.sub.6 H.sub.3O                                                                (CH.sub.2).sub.3                                       166a  C.sub.6 H.sub.5S (CH.sub.2).sub.3                                       167a  C.sub.6 H.sub.5CH.sub.2O                                                                       (CH.sub.2).sub.3                                       168a  C.sub.6 H.sub.5O (CH.sub.2).sub.4                                       169a  2-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.4                                       170a  3-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.4                                       171a  4-F C.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.4                                       172a  2-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.4                                       173a  3-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.4                                       174a  4-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.4                                       175a  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.4                                       176a  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.4                                       177a  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.4                                       178a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            (CH.sub.2).sub.4                                       179a  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                            (CH.sub.2).sub.4                                       180a  4-CF.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.4                                       181a  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                              (CH.sub.2).sub.4                                       182a  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4                                                    (CH.sub.2).sub.4                                       183a  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                 (CH.sub.2).sub.4                                       184a  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                         (CH.sub.2).sub.4                                       185a  1-naphthyl-O     (CH.sub.2).sub.4                                       186a  2-naphthyl-O     (CH.sub.2).sub.4                                       187a  3-CF.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.4                                       188a  3-iso-C.sub.3 H.sub.7C.sub.6 H.sub.4O                                                          (CH.sub.2).sub.4                                       189a  4-iso-C.sub.3 H.sub.7C.sub.6 H.sub.4O                                                          (CH.sub.2).sub.4                                       190a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            (CH.sub.2).sub.4                                       191a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            (CH.sub.2).sub.4                                       192a  3-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                              (CH.sub.2).sub.4                                       193a  2,4-Cl.sub.2C.sub.6 H.sub.3O                                                                   (CH.sub.2).sub.4                                       194a  3,4-Cl.sub.2C.sub.6 H.sub.3O                                                                   (CH.sub.2).sub.4                                       195a  3,5-Cl.sub.2C.sub.6 H.sub.3O                                                                   (CH.sub.2).sub.4                                       196a  2,6-Cl.sub.2C.sub.6 H.sub.3O                                                                   (CH.sub.2).sub.4                                       197a  2-Cl,4-CH.sub.3C.sub.6 H.sub.3O                                                                (CH.sub.2).sub.4                                       198a  2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                           (CH.sub.2).sub.4                                       199a  2,5-(CH.sub.3).sub.2C.sub.6 H.sub.3O                                                           (CH.sub.2).sub.4                                       200a  4-CNC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.4                                       201a  C.sub.6 H.sub.5S (CH.sub.2).sub.4                                       202a  C.sub.6 H.sub.5CH.sub.2O                                                                       (CH.sub.2).sub.4                                       203a  C.sub.6 H.sub.5O CH.sub.2CHCHCH.sub.2                                   204a  2-FC.sub.6 H.sub.4O                                                                            CH.sub.2CHCHCH.sub.2                                   205a  3-FC.sub.6 H.sub.4O                                                                            CH.sub.2CHCHCH.sub.2                                   206a  4-FC.sub.6 H.sub.4O                                                                            CH.sub.2CHCHCH.sub.2                                   207a  2-ClC.sub.6 H.sub.4O                                                                           CH.sub.2CHCHCH.sub.2                                   208a  3-ClC.sub.6 H.sub.4O                                                                           CH.sub.2CHCHCH.sub.2                                   209a  4-ClC.sub.6 H.sub.4O                                                                           CH.sub.2CHCH CH.sub.2                                  210a  C.sub.6 H.sub.5O (CH.sub.2).sub.5                                       211a  2-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.5                                       212a  3-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.5                                       213a  4-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.5                                       214a  2-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.5                                       215a  3-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.5                                       216a  4-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.5                                       217a  2-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.5                                       218a  3-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.5                                       219a  4-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.5                                       220a  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.5                                       221a  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.5                                       222a  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.5                                       223a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            (CH.sub.2).sub.5                                       224a  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                            (CH.sub.2).sub.5                                       225a  4-CF.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.5                                       226a  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                              (CH.sub.2).sub.5                                       227a  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                   (CH.sub.2).sub.5                                       228a  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                 (CH.sub.2).sub.5                                       229a  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                         (CH.sub.2).sub.5                                       230a  1-naphthyl-O     (CH.sub.2).sub.5                                       231a  2-naphthyl-O     (CH.sub.2).sub.5                                       232a  C.sub.6 H.sub.5CH.sub.2O                                                                       (CH.sub.2).sub.5                                       233a  C.sub.6 H.sub.5O (CH.sub.2).sub.6                                       234a  2-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.6                                       235a  3-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.6                                       236a  4-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.6                                       237a  2-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.6                                       238a  3-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.6                                       239a  4-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.6                                       240a  2-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.6                                       241a  3-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.6                                       242a  4-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.6                                       243a  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.6                                       244a  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.6                                       245a  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.6                                       246a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            (CH.sub.2).sub.6                                       247a  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                            (CH.sub.2).sub.6                                       248a  4-CF.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.6                                       249a  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                              (CH.sub.2).sub. 6                                      250a  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                   (CH.sub.2).sub.6                                       251a  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                 (CH.sub.2).sub.6                                       252a  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                         (CH.sub.2).sub.6                                       253a  1-naphthyl-O     (CH.sub.2).sub.6                                       254a  2-naphthyl-O     (CH.sub.2).sub.6                                       255a  C.sub.6 H.sub.5CH.sub.2O                                                                       (CH.sub.2).sub.6                                       256a  C.sub.6 H.sub.5O (CH.sub.2).sub.7                                       257a  2-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.7                                       258a  3-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.7                                       259a  4-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.7                                       260a  2-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.7                                       261a  3-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.7                                       262a  4-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.7                                       263a  2-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.7                                       264a  3-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.7                                       265a  4-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.7                                       266a  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.7                                       267a  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.7                                       268a  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.7                                       269a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            (CH.sub.2).sub.7                                       270a  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                            (CH.sub.2).sub.7                                       271a  4-CF.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.7                                       272a  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                              (CH.sub.2).sub.7                                       273a  2,4,6-(Cl.sub.3).sub.3C.sub.6 H.sub.2O                                                         (CH.sub.2).sub.7                                       274a  2,4,6-(CH.sub.3)C.sub.6 H.sub.2O                                                               (CH.sub.2).sub.7                                       275a  1-naphthyl-O     (CH.sub.2).sub.7                                       276a  2-naphthyl-O     (CH.sub.2).sub.7                                       277a  4-(C.sub.6 H.sub.5 CH.sub.2O)C.sub.6 H.sub.4O                                                  (CH.sub.2).sub.7                                       278a  C.sub.6 H.sub.5CH.sub.2O                                                                       (CH.sub.2).sub.7                                       279a  C.sub.6 H.sub.5O (CH.sub.2).sub.8                                       280a  2-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.8                                       281a  3-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.8                                       282a  4-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.8                                       283a  2-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.8                                       284a  3-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.8                                       285a  4-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.8                                       286a  2-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.8                                       287a  3-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.8                                       288a  4-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.8                                       289a  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.8                                       290a  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2 ).sub.8                                      291a  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.8                                       292a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            (CH.sub.2).sub.8                                       293a  4-C.sub.2 H.sub.5 OC.sub.6 H.sub.4O                                                            (CH.sub.2).sub.8                                       294a  4-CF.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.8                                       295a  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                              (CH.sub.2).sub.8                                       296a  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                   (CH.sub.2).sub.8                                       297a  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                 (CH.sub.2).sub.8                                       298a  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                         (CH.sub.2).sub.8                                       299a  1-naphthyl-O     (CH.sub.2).sub.8                                       300a  2-naphthyl-O     (CH.sub.2).sub.8                                       301a  C.sub.6 H.sub.5CH.sub.2O                                                                       (CH.sub.2).sub.8                                       302a  C.sub.6 H.sub.5O (CH.sub.2).sub.9                                       303a  C.sub.6 H.sub.5O (CH.sub.2).sub.10                                      304a  2-ClC.sub. 6 H.sub.4O                                                                          (CH.sub.2).sub.10                                      305a  3-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.10                                      306a  4-ClC.sub.6 H.sub.4O                                                                           (CH.sub.2).sub.10                                      307a  2-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.10                                      308a  3-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.10                                      309a  4-FC.sub.6 H.sub.4O                                                                            (CH.sub.2).sub.10                                      310a  2-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.10                                      311a  3-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.10                                      312a  4-CH.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.10                                      313a  2-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.10                                      314a  3-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.10                                      315a  4-CH.sub.3 OC.sub.6 H.sub.4O                                                                   (CH.sub.2).sub.10                                      316a  4-t-C.sub.4 H.sub.9C.sub.6 H.sub.4O                                                            (CH.sub.2).sub.10                                      317a  4-C.sub.2 H.sub.5 OC.sub.6 H.sub. 4O                                                           (CH.sub.2).sub.10                                      318a  4-CF.sub.3C.sub.6 H.sub.4O                                                                     (CH.sub.2).sub.10                                      319a  4-C.sub.6 H.sub.5C.sub.6 H.sub.4O                                                              (CH.sub.2).sub.10                                      320a  4-(C.sub.6 H.sub.5CH.sub.2O)C.sub.6 H.sub.4O                                                   (CH.sub.2).sub.10                                      321a  2,4,6-Cl.sub.3C.sub.6 H.sub.2O                                                                 (CH.sub.2).sub.10                                      322a  2,4,6-(CH.sub.3).sub.3C.sub.6 H.sub.2O                                                         (CH.sub.2).sub.10                                      323a  1-naphthyl-O     (CH.sub.2).sub.10                                      324a  2-naphthyl-O     (CH.sub.2).sub.10                                      325a  C.sub.6 H.sub.5CH.sub.2O                                                                       (CH.sub.2).sub.10                                      __________________________________________________________________________

Generally speaking, the novel compounds are extremely effective on abroad spectrum of phytopathogenic fungi, in particular those from theAscomycetes and Basidiomycetes classes. Some of them have a systemicaction and can be used as foliar and soil fungicides.

The fungicidal compounds are of particular interest for controlling alarge number of fungi in various crops or their seeds, especially wheat,rye, barley, oats, rice, Indian corn, lawns, cotton, soybeans, coffee,sugar cane, fruit and ornamentals in horticulture and viticulture, andin vegetables such as cucumbers, beans and cucurbits.

The novel compounds are particularly useful for controlling thefollowing plant diseases:

Erysiphe graminis in cereals,

Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,

Podosphaera leucotricha in apples,

Uncinula necator in vines,

Puccinia species in cereals,

Rhizoctonia species in cotton and lawns,

Ustilago species in cereals and sugar cane,

Venturia inaequalis (scab) in apples,

Helminthosporium species in cereals,

Septoria nodorum in wheat,

Botrytis cinerea (gray mold) in strawberries and grapes,

Cercospora arachidicola in groundnuts,

Pseudocercosporella herpotrichoides in wheat and barley,

Pyricularia oryzae in rice,

Phytophthora infestans in potatoes and tomatoes,

Fusarium and Verticillium species in various plants,

Plasmopara viticola in grapes,

Alternaria species in fruit and vegetables.

The compounds are applied by spraying or dusting the plants with theactive ingredients, or treating the seeds of the plants with the activeingredients. They may be applied before or after infection of the plantsor seeds by the fungi.

The novel substances can be converted into conventional formulationssuch as solutions, emulsions, suspensions, dusts, powders, pastes andgranules. The application forms depend entirely on the purposes forwhich they are intended; they should at all events ensure a fine anduniform distribution of the active ingredient. The formulations areproduced in known manner, for example by extending the active ingredientwith solvents and/or carriers, with or without the use of emulsifiersand dispersants; if water is used as solvent, it is also possible toemploy other organic solvents as auxiliary solvents. Suitableauxiliaries for this purpose are solvents such as aromatics (e.g.,xylene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g.,crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g.,cyclohexanone), amines (e.g., ethanolamine, dimethylformamide), andwater; carriers such as ground natural minerals (e.g., kaolins,aluminas, talc and chalk) and ground synthetic minerals (e.g., highlydisperse silica and silicates); emulsifiers such as nonionic and anionicemulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and aryl sulfonates); and dispersants such as lignin, sulfitewaste liquors and methylcellulose.

The fungicidal agents generally contain from 0.1 to 95, and preferablyfrom 0.5 to 90, wt % of active ingredient. The application rates arefrom 0.02 to 3 kg or more of active ingredient per hectare, depending onthe type of effect desired. The novel compounds may also be used forprotecting materials, for example against Paecilomyces variotii.

The agents and the ready-to-use formulations prepared from them, such assolutions, emulsions, suspensions, powders, dusts, pastes and granules,are applied in conventional manner, for example by spraying, atomizing,dusting, scattering, dressing or watering.

Examples of formulations are given below.

I. 90 parts by weight of compound no. 2 is mixed with 10 parts by weightof N-methyl-α-pyrrolidone. A mixture is obtained which is suitable forapplication in the form of very fine drops.

II. 20 parts by weight of compound no. 3 is dissolved in a mixtureconsisting of 80 parts by weight of xylene, 10 parts by weight of theadduct of 8 to 10 moles of ethylene oxide and 1 mole of oleicacid-N-monoethanolamide, 5 parts by weight of the calcium salt ofdodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40moles of ethylene oxide and 1 mole of castor oil. By pouring thesolution into water and uniformly distributing it therein, an aqueousdispersion is obtained.

III. 20 parts by weight of compound no. 4 is dissolved in a mixtureconsisting of 40 parts by weight of cyclohexanone, 30 parts by weight ofisobutanol, 20 parts by weight of the adduct of 40 moles of ethyleneoxide and 1 mole of castor oil. By pouring the solution into water andfinely distributing it therein, an aqueous dispersion is obtained.

IV. 20 parts by weight of compound no. 6 is dissolved in a mixtureconsisting of 25 parts by weight of cyclohexanol, 65 parts by weight ofa mineral oil fraction having a boiling point between 210° and 280° C.,and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1mole of castor oil. By pouring the solution into water and uniformlydistributing it therein, an aqueous dispersion is obtained.

V. 80 parts by weight of compound no. 13 is well mixed with 3 parts byweight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 10parts by weight of the sodium salt of a lignin-sulfonic acid obtainedfrom a sulfite waste liquor, and 7 parts by weight of powdered silicagel, and triturated in a hammer mill. By uniformly distributing themixture in water, a spray liquor is obtained.

VI. 3 parts by weight of compound no. 19 is intimately mixed with 97parts by weight of particulate kaolin. A dust is obtained containing 3%by weight of the active ingredient.

VII. 30 parts by weight of compound no. 2 is intimately mixed with amixture consisting of 92 parts by weight of powdered silica gel and 8parts by weight of paraffin oil which has been sprayed onto the surfaceof this silica gel. A formulation of the active ingredient is obtainedhaving good adherence.

VIII. 40 parts by weight of compound no. 3 is intimately mixed with 10parts by weight of the sodium salt of a phenolsulfonicacid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts ofwater to give a stable aqueous dispersion. Dilution in water gives anaqueous dispersion.

IX. 20 parts by weight of compound no. 4 is intimately mixed with 2parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8parts by weight of a fatty alcohol polyglycol ether, 2 parts by weightof the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensateand 68 parts by weight of a paraffinic mineral oil. A stable oilydispersion is obtained.

In these application forms, the agents according to the invention mayalso be present together with other active ingredients, for exampleherbicides, insecticides, growth regulators, and fungicides, and mayfurthermore be mixed and applied together with fertilizers. Admixturewith other fungicides frequently results in an increase in thefungicidal spectrum.

USE EXAMPLES

For comparison purposes, methyl 2-benzyloxyphenylglyoxylateO-methyloxime (A) disclosed in EP 253,213 was used.

USE EXAMPLE 1 Action on Botrytis Cinerea in Pimientos

Pimiento seedlings of the "Neusiedler Ideal Elite" variety with 4 to 5well developed leaves were sprayed to runoff with aqueous suspensionscontaining (dry basis) 80% of active ingredient and 20% of emulsifier.After the sprayed-on layer had dried, the plants were sprayed with aconidial suspension of the fungus Botrytis cinerea and kept in ahigh-humidity chamber at 22° to 24° C. After 5 days, the disease hadspread on the untreated control plants to such an extent that thenecroses covered the major portion of the leaves.

The results show that active ingredients 6 and 13, applied as 0.05 wt %spray liquors, have a better fungicidal action (90%) than prior artactive ingredient A (65%).

USE EXAMPLE 2 Action on Pyrenophora Teres

Barley seedlings of the "Igri" variety were sprayed to runoff at thetwo-leaf stage with aqueous suspensions consisting (dry basis) of 80% ofactive ingredient and 20% of emulsifier. After 24 hours the plants wereinoculated with a spore suspension of the fungus Pyrenophora teres, andset up for 48 hours in a high-humidity climatic cabinet at 18° C. Theplants were then cultivated for a further 5 days in the greenhouse at20° to 22° C. and a relative humidity of 70° C. The extent of fungusspread was then assessed.

The results show that active ingredients 2, 3, 4, 6, 13 and 19, appliedas 0.05 wt % spray liquors, have a better fungicidal action (90%) thanprior art active ingredient A (60%).

We claim:
 1. Ortho-substituted 1-naphthyl ethers of the general formulaI ##STR11## where X is N, Y is saturated or unsaturated C₁ -C₁₂-alkylene and R is aryl, aryloxy, arylthio or arylalkoxy, it beingpossible for the aromatic ring to be substituted one to five times bythe following: halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₄-alkylthio, C₁ -C₂ -haloalkyl, aryl, aryl-C₁ -C₂ -alkoxy, C₁ -C₄-alkylcarbonyl, amino which is substituted once or twice by C₁ -C₄-alkyl, or is cyano or nitro.
 2. A process for combating fungi, whereinthe fungi or the materials, plants, seed or soil threatened by fungusattack are treated with a fungicidally effective amount of a compound ofthe formula I ##STR12## where X is N, Y is saturated or unsaturated C₁-C₁₂ -alkylene and R is aryl, aryloxy, arylthio or arylalkoxy, it beingpossible for the aromatic ring to be substituted one to five times bythe following: halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₄-alkylthio, C₁ -C₂ -haloalkyl, aryl, aryl-C₁ -C₂ -alkoxy, C₁ -C₄-alkylcarbonyl, amino which is substituted once or twice by C₁ -C₄-alkyl, or is cyano or nitro.
 3. A fungicide containing an inert carrierand a fungicidally effective amount of a compound of the formula I##STR13## where X is N, Y is saturated or unsaturated C₁ -C₁₂ -alkyleneand R is aryl, aryloxy, arylthio or arylalkoxy, it being possible forthe aromatic ring to be substituted one to five times by the following:halogen, C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₂-haloalkyl, aryl, aryl-C₁ -C₂ -alkoxy, C₁ -C₄ -alkylcarbonyl, aminowhich is substituted once or twice by C₁ -C₄ -alkyl, or is cyano ornitro.
 4. A compound of the formula I as set forth in claim 1, where Ris 2-fluorophenyl, Y is CH₂ and X is N.
 5. A compound of the formula Ias set forth in claim 1, where R is 2-chlorophenyl Y is CH₂ and X is N.6. A compound of the formula I as set forth in claim 1, where R is2-bromophenyl, Y is CH₂ and X is N.